In the rulebooks of how to age gracefully the don’ts make a lot more noise than the dos. No leather trousers! No cleavage! No man buns! Our skateboards! The list of items allegedly verboten for the over-50s is endless. Your life has been boobytrapped, one false move and the world will fall about laughing. It’s enough to make your hair go gray – oh, wait.
Here’s a better idea. Let’s talk about how to dress right for your age, rather than how to avoid getting it wrong. The list of style icons over 50 gets longer every year, and between them they are tearing up the rulebook (except the one about skateboards, sorry). Iris Apfel, White House interior designer turned fashion influencer, filled her recent capsule collection for H&M with fringed violet jacquard miniskirts and frog-shaped rhinestone earrings, and it sold out in hours. Apfel turns 101 this year.
“You have to dress for yourself before you dress for your age,” Apfel once said. Actually I think the trick is to recognize that the two are the same. Dress for the person you are now. There is no reason to cosplay as an imaginary Wise Elder version of yourself, but neither do you need to dress as the person you were 15 years ago. Look, I’m not doubting that you are still super fun at parties but let’s say – just for the sake of argument – that these days you also quite enjoy getting up early on a Saturday to walk the dog before the park gets busy. That’s who you are now and that person may find a nice pair of corduroys more useful than leather trousers. Here’s how to get it right.
Dress up, not down
When you are 22, jeans and a black T-shirt looks effortless and slightly mysterious, but 30 years later, the same outfit can make you invisible. This is why, topsy turvy as it sounds, getting older calls for clothes that shout a bit louder. Go 10% more dressy for every 10 years over 40. There are different ways you can dial up your wardrobe. You can make it smarter and more formal – swap T-shirts for collared shirts, floppy cardigans for tailored jackets – or you can keep it casual but add color and texture to make it glam-casual rather than scruffy. There comes a time in the life of every 50-ish being when you realize that the Main Character Energy has gravitated toward the generation below, and therefore you have to work a bit harder not to fade into the background. This doesn’t mean you have to go full Tilda Swinton and wear something architectural and tangerine colored every day, just that jeans and a T-shirt may not cut it.
But don’t go changing too much
My mum, a very chic 74, says that her secret is wearing what she has always worn – sort of. “I’ve always loved dresses, and I still do. The hemlines are a meter longer than they were 40 years ago, that’s all.” A radical change of style direction is inadvisable at this point. If you have made it through your first half century in jeans and trainers, a complete Savile Row makeover at this point will almost certainly be an expensive mistake. Start by swapping that bobbly zip-up fleece for an unstructured blazer and take it from there. If you have always been a Phoebe Philo-worshipping, navy-and-polo neck type you don’t have to start wearing purple and fun brooches to show that you still appreciate fashion. Channel Lee Radziwill and keep it refined and understated with a few strategic additions of jewellery.
Be a silver fox
Gray is the new blonde. Silver foxes (and vixens) have more fun. Andie MacDowell (64) ruled the Cannes red carpet with her gray hair last year; Kristen McMenamy (57) made the cover of British Vogue with long silver locks a few months ago. Idris Elba (49) has a salt-and-pepper beard these days and even Cillian Murphy as Tommy Shelby was graying at the temples by the finale of Peaky Blinders. The convention that once dictated women must cut their hair in midlife if they were to avoid being shamed as “mutton dressed as lamb” – the 20th-century equivalent of witch-hunting – has thankfully died out. It remains true, however, that good grooming becomes essential as you get older, for men and women. The same level of devil-may-care scruffiness that looks deliciously rock’n’roll at 25 will make a 55-year-old appear to be falling apart at the seams. Ponytails on men and plaits on women are dabbled with at your own risk in midlife, but you do you.
Leather trousers: proceed with caution
At 58, Brad Pitt is a year older than Boris Johnson. I share this fact with you to illustrate that there are no hard and fast rules about what you can get away with at what age. There is no doubt that Pitt could pull off a pair of leather trousers if he wanted to, but as for Johnson in leather, well I can only apologise for conjuring that image. See also: ripped jeans, overzealous shirt-unbuttoning (men and women), band T-shirts, anything with a skull motif on it.
If you are a man in the half-century ballpark, then you are of an age when the shirt worn under a crewneck or v-neck sweater has been a go-to smart-casual office look for most of your working life. But there may come a day when you look in the mirror and realize that your shirt (it’s probably pale blue) under a sweater (I’m thinking, charcoal grey) looks less like you are about to wow a Silicon Valley boardroom and more like you are ready to ease into your favorite chair with a hardback historical biography. Try wearing a jacket instead. (Bill Nighy gives good jacket-over-casual-shirt, no tie.) For women, trousersuits are excellent at all ages (see: Viola Davis) but if tailoring isn’t for you, then think Prada. Not what Miuccia Prada puts on the catwalk, but what she herself wears: a neatly fitted sweater, a knee- or calf-length A-line or printed skirt, kitten heels, very good jewellery.
Now that 40th birthdays seem to mostly be all-night raves, 50 and upwards might be the first time you have to do grown-up eveningwear. Figuring out what to wear is almost as stressful as the anticipation of the hangover, which now lasts three days. For men, the party shirt is still a safe choice, but nothing shiny, no Hawaiian florals and, whatever happens, do not take it off on the dancefloor. For women, if déhabillé has been your signature, take a steer from Carine Roitfeld who shows that messy black eyeliner and leather skirts still work at 67 when worn with a simple silk blouse and black sandals. Experiment with floorlength: a kaftan-adjacent maxidress is pleasingly tall, and you can wear flat shoes. Oprah Winfrey in a floor-length shirt dress is your key reference here, not the Duchess of Devonshire.
Taking the same three dresses on holiday for 25 years on the trot is a great British tradition and sustainable to boot, so it’s a green light for the denim mini you bought at the big Topshop when Tony Blair was in Downing Street and the kaftan you bought on Benirrás beach in Ibiza because a twentysomething Sienna Miller was wearing one. But as a rule of thumb, if you now have to take your reading glasses out to dinner and/or use the torch function on your phone to read menus, go easy on the cheesecloth and embroidery and gathered milkmaid necklines. Relaxed and boho is good, but droopy is not a vibe we want to emphasize at this juncture. White jeans are always a good idea. Men: classic sunglasses in black or tortoiseshell only, as anything mirrored will now make you look like a grizzled LAPD cop.
OK, there are a couple don’ts
I can’t lie, there are a couple of red lines. For women: sweatshirts or tote bags with cutesy whimsical slogans that include the words “prosecco” or “yoga”. For men: cycling outfits with an excessive volume of lime green. I concede that I’m not really qualified to stand in judgment on cycling gear seeing as how I’ve only been on a bike once since graduating, but can it really be necessary to go full Ninja Turtle to pedal around Regent’s Park?